Spontaneous paraesophageal hematoma (SPH) likely shares a common etiology with spontaneous intramural esophageal hematoma (IEH). Patients with IEH typically present with hematemesis or melena leading to early detection and management, but patients with SPH do not have overt gastrointestinal bleeding on presentation. Management depends on the correction of the underlying causative factor. We present the first case of a spontaneous paraesophageal hematoma in a patient with hemophilia B. Awareness of this complication of hemophilia, its clinical manifestations, and imaging findings, allows for a timely diagnosis and appropriate management.